Lithium Hydroxide → N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxyacetamide

HRID 1923747Notes

Reaction equation

HRID 1923747 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C.[Br:29][C:30]1[C:31]([F:40])=[C:32]2[C:38]([NH2:39])=[CH:37][NH:36][C:33]2=[N:34][CH:35]=1.[Li+].[OH-].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:29][C:30]1[C:31]([F:40])=[C:32]2[C:38]([NH:39][C:4](=[O:6])[CH2:3][O:2][CH3:1])=[CH:37][NH:36][C:33]2=[N:34][CH:35]=1

Participants

8

Reactant 6

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 12251Methoxyacetic AcidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205365N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxyacetamideYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxyacetic acid (313 mg, 3.5 mmol), bis(2-oxooxazolidin-3-yl)phosphinic chloride (885 mg, 3.5 mmol) and triethylamine (880 mg, 8.7 mmol) were added to 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (400 mg, 1.7 mmol, Example 1, Step H) in DCM (50 mL). The reaction was stirred at room temperature for 1 hour, and then 3M aqueous LiOH (4 mL) was added. The reaction was stirred for 1 hour, and then saturated aqueous Na2CO3 was added (200 mL). The aqueous phase was extracted 3 times with DCM (200 mL), and then the combined organic phases were dried over MgSO4 and concentrated to dryness. N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxyacetamide (236 mg, 45% yield) was isolated as a solid.

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. extractionThe aqueous phase was extracted 3 times with DCM (200 mL)
  3. dry with materialthe combined organic phases were dried over MgSO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-588bcbed44624764983afdd6e106a472
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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